Acetic Acid → HCID 86754585, compound

HRID 1738748Notes

Reaction equation

HRID 1738748 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O-:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([N+:14]1[C:18]2[CH:19]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=[CH:22][C:17]=2[S:16][C:15]=1[CH3:29])[CH3:13].O=[C:31]1[CH2:38][C:35]([CH3:37])([CH3:36])[CH2:34][C:33]([CH3:39])=[CH:32]1.C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1.O>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[CH2:12]([N+:14]1[C:18]2[CH:19]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=[CH:22][C:17]=2[S:16][C:15]=1[CH:29]=[C:31]1[CH2:38][C:35]([CH3:37])([CH3:36])[CH2:34][C:33]([CH3:39])=[CH:32]1)[CH3:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6544IsophoroneHCID 517165Ammonium AcetateHCID 86754586HCID 86754586, compound

Product 1

HCID 86754585HCID 86754585, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4.3 g of 3-ethyl-2-methyl-5-phenylbenzothiazolium paratoluene sulfonate, 2.7 ml of isophorone, 1 g of ammonium acetate and 3.4 ml of acetic acid were dissolved in 35 ml of toluene and then heated under reflux for 1.5 hours while removing water by azeotropy. After leaving the solution standing to cool to room temperature, 50 ml of water was added. The resulting solution was extracted by 50 ml of methylene chloride, the organic layer was dried over sodium sulfate, the solvent was distilled off, 30 ml of ethyl acetate was added, and 4.7 g of 3-ethyl-2-(3,5,5-trimethyl-2-cyclohexenylidene)methyl-5-phenylbenzothiazolium paratoluene sulfonate produced as a solid was collected by filtration. 4.7 g of the solid obtained and 4.2 g of 1,3-diphenyl-1,3-diazapropene were dissolved in 20 ml of acetic anhydride, the reaction solution was heated under reflux for 8 hours and then left standing to cool to room temperature, 5 g of sodium iodide and 50 ml of water were added, and the resulting solution was extracted by methylene chloride. The organic layer was dried over sodium sulfate and the solvent was distilled off to obtain 2.9 g of 3-ethyl-2-[3-(2-acetanilidoethenyl)-5,5-dimethyl-2-cyclohexenylidene]methyl-5-phenylbenzothiazolium iodide salt as a solid. 0.7 g of the solid obtained and 0.6 g of 2-methyl-3-[2-(1-naphthoxy)ethyl]-5-phenylbenzothiazolium paratoluene sulfonate were dissolved in 10 ml of pyridine at 80° C., and thereto 1 ml of triethylamine was added. The reaction solution was stirred at room temperature for 1 hour, and 30 ml of ethyl acetate was added thereto. The crude crystals produced were collected by filtration and then recrystallized from methylene chloride and isopropyl alcohol to obtain 0.2 g of Compound 39.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. customwhile removing water by azeotropy
  4. customAfter leaving the solution
  5. extractionThe resulting solution was extracted by 50 ml of methylene chloride
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. distillationthe solvent was distilled off
  8. addition30 ml of ethyl acetate was added

Sources & evidence

ORD record
ord-bd676a40c4fb47a2802db299dd5af049
Source dataset
uspto-grants-1999_10
Patent number
US05965346

Reaction notes

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